Fungicidal active substance combinations

ABSTRACT

The invention relates to novel fungicidally active compound combinations of 2′-cyano-3,4-dichloroisothiazole-5-carboxanilide of the formula  
                 
and active compounds listed in the disclosure.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP2004/008072, filed Jul. 20, 2004,which was published in German as International Patent Publication WO2005/009130 on Feb. 3, 2005, and is entitled to the right of priority ofGerman Patent Application 103 33 373.8, filed Jul. 23, 2003.

The invention relates to active compound combinations which comprise theknown 2′-cyano-3,4-dichloroisothiazole-5-carboxanilide on the one handand other known fungicidally active compounds on the other hand, andwhich are highly suitable for controlling phytopathogenic fungi.

It is already known that2′-cyano-3,4-dichloroisothiazole-5-carboxanilide has fungicidalproperties (cf. WO 99-024 413). The activity of this substance is good;however, at low application rates it is in some cases unsatisfactory.

Furthermore, it is already known that numerous triazole derivatives,strobilurins, aniline derivatives, carboxamides and various heterocyclescan be used for controlling fungi (cf. EP-A 0 040 345, DE-A 2 234 010,EP-A 0 382 375, EP-A 0 515 901 and Pesticide Manual, 9th. Edition(1991), pages 391, 506, 746 and 846). However, the activity of thesesubstances at low application rates is likewise not always sufficient.

It has now been found that the novel active compound combinationsconsisting of 2′-cyano-3,4-dichloroisothiazole-5-carboxanilide of theformula

-   (1)    N-[1-(4-chlorophenyl)ethyl]-2,2-dichloro-1-ethyl-3-methylcyclopropane-carboxamide    of the formula-   (2) a strobilurin derivative of the formula-   (3) a triazole derivative of the formula-   (4) a phenylurea derivative of the formula-   (5) the chlorophthalide of the formula-   (6) the hydrazine derivative of the formula-   (7) the benzothiazole derivative of the formula-   (8) the cyanocarboxamide of the formula-   (9) a carboxamide derivative of the formula-   (10) the quinolone derivative of the formula-   (11) the dithiolane derivative of the formula-   (12) the phosphorus compound of the formula-   (13) the iminoglycine derivative of the formula    have very good fungicidal properties.

Surprisingly, the fungicidal activity of the active compoundcombinations according to the invention is considerably higher than thesum of the activities of the individual active compounds. Thus, anunforeseeable, true synergistic effect is present, and not just anaddition of activities.

2′-Cyano-3,4-dichloroisothiazole-5-carboxanilide of the formula (I) isknown (cf. WO 99-24 413).

From the structural formula of the active compound of the formula (II)it can be seen that the compound has three asymmetrically substitutedcarbon atoms. Accordingly, the product can be present as a mixture ofdifferent isomers or else in the form of a single component. Particularpreference is given to the compounds

N—(R)-[1-(4-chlorophenyl)ethyl]-(1S,3R)-2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamideof the Formula

N—(R)-[1-(4-chlorophenyl)ethyl]-(1R,3S)-2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamideof the Formula

The mixture of the substances of the formulae (IIa) and (IIb) is knownunder the common name carpropamid.

Prothioconazole is mainly present in the “thiono” form of the formula(IV-c) given above. However, it can also be present in the tautomeric“mercapto” form of the formula

For the sake of simplicity, only the “thiono” form is shown in eachcase.

The compounds present in addition to the active compound of the formula(I) in the active compound combinations according to the invention arelikewise known. Specifically, the active compounds are described in thefollowing publications:

(1) compounds of the formula (II) and individual isomers thereof

-   -   EP-A 0 341 475        (2) compounds of the formulae (III-a) to (III-d)    -   EP-A 0 382 375    -   DE-A 195 39 324    -   EP-A 0 398 692    -   WO 98-21 189        (3) compounds of the formulae (IV-a) to (IV-c)    -   DE-A 2 324 010    -   EP-A 0 040 345    -   WO 96-16 048        (4) compound of the formula (V)    -   DE-A 2 732 257        (5) compound of the formula (VI)    -   Pesticide Manual, 9th Edition    -   (1991), page 801        (6) compound of the formula (VII)    -   Pesticide Manual, 9th Edition    -   (1991), page 391        (7) compound of the formula (VIII)    -   Pesticide Manual, 9th Edition    -   (1991), page 846        (8) compound of the formula (IX)    -   JP-A 07-206 608        (9) compounds of the formulae (X-a) and (X-b)    -   EP-A 0 371 950    -   EP-A 0 315 502        (10) compound of the formula (XI)    -   Pesticide Manual, 9th Edition    -   (1991), page 746        (11) compound of the formula (XII)    -   Pesticide Manual, 9th Edition    -   (1991), page 506        (12) compound of the formula (XIII)    -   DE-A 2 456 627        (13) compound of the formula (XIV)    -   Pesticide Manual, 9th Edition    -   (1991), page 515

In addition to the active compound of the formula (I), the activecompound combinations according to the invention comprise at least oneactive compound of the compounds of groups (1) to (13). In addition,they may also comprise further fungicidally or insecticidally activeadditives.

The synergistic effect is particularly pronounced when the activecompounds in the active compound combinations according to the inventionare present in certain weight ratios. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range. In general,

from 0.1 to 20 parts by weight, preferably from 0.2 to 10 parts byweight, of active compound of group (1),

from 0.1 to 20 parts by weight, preferably from 0.2 to 10 parts byweight, of active compound of group (2),

from 0.01 to 50 parts by weight, preferably from 0.02 to 20 parts byweight, of active compound of group (3),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (4),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (5),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (6),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (7),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (8),

from 0.01 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (9),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (10),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (11),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (12),

from 0.1 to 100 parts by weight, preferably from 0.2 to 50 parts byweight, of active compound of group (13),

per part by weight of active compound of the formula (I).

The active compound combinations according to the invention have verygood fungicidal properties and can be employed for controllingphytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes,Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes,Deuteromycetes, etc.

The active compound combinations according to the invention areparticularly suitable for controlling cereal and rice diseases, such asPyricularia, Cochliobolus, Leptosphaeria, Rhizoctonia, Septoria,Pyrenophora, Pseudocercosporella, Erysiphe, Puccinia and Fusarium, andfor controlling diseases encountered in viticulture, such as Uncinula,Plasmopara and Botrytis, and furthermore in dicotyledonous crops forcontrolling powdery and downy mildew fungi and causative organisms ofleaf spot.

The fact that the active compound combinations are well tolerated byplants at the concentrations required for controlling plant diseasespermits the treatment of above-ground parts of plants, of propagationstock and seeds, and of the soil. The active compound combinationsaccording to the invention can be employed for foliar application orelse as seed dressings.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof, are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove.

With particular preference, plants of the plant cultivars which are ineach case commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (traits) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, biotypes or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(synergistic) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (traits) to these plants. Examples of such propertiesare better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, tobacco and oilseed rape.Traits that are emphasized are in particular increased defence of theplants against insects, spiders, nematodes and slugs and snails bytoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c,Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidal active compounds, for example imidazolinones, sulphonylureas,glyphosate or phosphinotricin (for example the “PAT” gene). The geneswhich impart the desired traits in question can also be present incombination with one another in the transgenic plants. Examples of “Btplants” which may be mentioned are maize varieties, cotton varieties,soya bean varieties and potato varieties which are sold under the tradenames YIELD GARD® (for example maize, cotton, soya beans), KnockOut®(for example maize), StarLink® (for example maize), Bollgard® (cotton),Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerantplants which may be mentioned are maize varieties, cotton varieties andsoya bean varieties which are sold under the trade names Roundup Ready®(tolerance to glyphosate, for example maize, cotton, soya beans),Liberty Link® (tolerance to phosphinotricin, for example oilseed rape),IMI® (tolerance to imidazolinones) and STS® (tolerance tosulphonylureas, for example maize). Herbicide-resistant plants (plantsbred in a conventional manner for herbicide tolerance) which may bementioned also include the varieties sold under the name Clearfield®(for example maize). Of course, these statements also apply to plantcultivars which have these genetic traits or genetic traits still to bedeveloped and which will be developed and/or marketed in the future.

The plants listed can be treated in a particularly advantageous mannerwith the active compound mixtures according to the invention. Thepreferred ranges stated above for the mixtures also apply to thetreatment of these plants.

The active compound combinations according to the invention can beconverted to the customary formulations, such as solutions, emulsions,suspensions, powders, foams, pastes, granules, aerosols,microencapsulations in polymeric substances and into coatingcompositions for seed, and ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds or active compound combinations with extenders,that is liquid solvents, liquefied gases under pressure, and/or solidcarriers, optionally with the use of surfactants, that is emulsifiersand/or dispersants, and/or foam formers. If the extender used is water,it is also possible to use, for example, organic solvents as auxiliarysolvents. Suitable liquid solvents include, essentially: aromatics suchas xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water. Liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellants such as butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compounds, preferably between 0.5 and 90%.

The compounds (I) and (II) to (XIV) can be applied together, that isjointly or separately, or in succession, the sequence in the case ofseparate application generally not having any effect on the controlresults.

In the formulations, the active compound combinations according to theinvention can be present as a mixture with other known active compoundssuch as fungicides, insecticides, acaricides and herbicides, and asmixtures with fertilizers or plant growth regulators.

Examples of suitable mixing components are the following compounds:

Fungicides:

2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl;actinovate; aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium;andoprim; anilazine; azaconazole; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; boscalid;bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulphide;capsimycin; captafol; captan; carbendazim; carboxin; carvone;chinomethionat; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole;cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone;dichlorophen; diclomezine; dicloran; diethofencarb; difenoconazole;diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole;diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos;dithianon; dodine; drazoxolon; edifenphos; epoxiconazole; ethaboxam;ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol;fenbuconazole; fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil;fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine;fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin;fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;flutriafol; folpet; fosetyl-sodium; fuberidazole; furalaxyl;furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole;hymexazol; imazalil; imibenconazole; iminoctadine triacetate;iminoctadine tris(albesilate); iodocarb; ipconazole; iprobenfos;iprodione; iprovalicarb; irumamycin; isovaledione; kresoxim-methyl;mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl;metalaxyl-M; metconazole; methasulfocarb; methfuroxam; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;methyl2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyl]-.alpha.-(methoxymethylene)benzeneacetate;methyl2-[2-[3-(4-chlorophenyl)-1-methyl-allylideneaminooxymethyl]phenyl]-3-methoxyacrylate;metiram; metrafenone; metsulfovax; mildiomycin; monopotassium carbonate;myclobutanil; myclozolin; nabam,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxy-benzamide;N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decan-3-amine; natamycin;nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin;oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin;paclobutrazol; pefurazoate; penconazole; penthiopyrad; phosdiphen;picobenzamid; picoxystrobin; piperalin; polyoxins; polyoxorim;probenazole; prochloraz; procymidone; propamocarb; propanosine-sodium;propiconazole; propineb; proquinazid; pyraclostrobin; pyrazophos;pyrifenox; pyrimethanil; pyroxyfur; pyrrolnitrine; quinconazole;quinoxyfen; quintozene; silthiofam; simeconazole; sodiumtetrathiocarbonate; spiroxamine; sulphur; tecloftalam; tecnazene;tetcyclacis; tetraconazole; thiabendazole; thicyofen;thiophanate-methyl; thiram; tiadinil; tioxymid; tolclofos-methyl;tolylfluanid; triadimefon; triazbutil; triazoxide; tricyclamide;tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide;(2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]-butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine;2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)phenyl]-ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,3-triazol-3-one;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile;3-[(3-bromo-6-fluoro-2-methyl-1H-indol-1-yl)sulphonyl]-N,N-dimethyl-1H-1,2,4-triazole-1-sulphonamide;

and also copper salts and copper preparations, such as Bordeaux mixture;copper hydroxide; copper naphthenate; copper oxychloride; coppersulphate; cufraneb; copper(I) oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin(alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541,azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl,azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, Bacillus thuringiensis strain EG-2348, Bacillusthuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821,baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb,benfuracarb, bensultap, benzoximate, beta-cyfluthrin, beta-cypermethrin,bifenazate, bifenthrin, binapacryl, bioallethrin,bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl,bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb,buprofezin, butathiofos, butocarboxim, butoxycarboxim, butyl-pyridaben,

cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,carbosulfan, cartap, CGA-50439, chinomethionat, chlordane,chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl),chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin,clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene,cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyphenothrin (1R-transisomer), cyromazine,

DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphone,diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, dicofol,dicrotophos, dicyclanil, diflubenzuron, dimethoate, dimethylvinphos,dinobuton, dinocap, dinotefuran, diofenolan, disulfoton, docusat-sodium,dofenapyn, DOWCO-439,

eflusilanate, emamectin, emamectin-benzoate, empenthrin (1R-isomer),endosulfan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb,ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,

famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin,fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb,fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fensulfothion,fenthion, fentrifanil, fenvalerate, fipronil, flonicamid, fluacrypyrim,fluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flucythrinate,flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos,flutenzin (flufenzine), fluvalinate, fonofos, formetanate, formothion,fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb,

gamma-HCH, gossyplure, grandlure, granulosis viruses,

halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,hexythiazox, hydramethylnone, hydroprene,

IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos,iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin,

japonilure,

kadethrin, nuclear polyhedrosis viruses, kinoprene,

lambda-cyhalothrin, lindane, lufenuron,

malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium,methacrifos, methamidophos, Metharhizium anisopliae, Metharhiziumflavoviride, methidathion, methiocarb, methomyl, methoprene,methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin,MTI-800,

naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine,nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768,novaluron, noviflumuron,

OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl,oxydemeton-methyl,

Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl),permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-transisomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl,pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos,propargite, propetamphos, propoxur, prothiofos, prothoate,protrifenbute, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridalyl, pyridaphenthion, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,

S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad,spirodiclofen, spiromesifen, sulfluramid, sulfotep, sulprofos, SZI-121,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos,teflubenzuron, tefluthrin, temephos, temivinphos, terbam, terbufos,tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin (1R-isomer),tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin,tralomethrin, transfluthrin, triarathene, triazamate, triazophos,triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, verbutin, Verticillium lecanii,

WL-108477, WL-40027,

YI-5201, YI-5301, YI-5302,

XMC, xylylcarb,

ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,

the compound 3-methylphenyl propylcarbamate (tsumacide Z),

the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-octane-3-carbonitrile(CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg.No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),

and also preparations which comprise insecticidally active plantextracts, nematodes, fungi or viruses.

The active compound combinations can be used as such, in the form oftheir formulations or as the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, spreading, and as a powder for dry seedtreatment, a solution for seed treatment, a water-soluble powder forseed treatment, a water-soluble powder for slurry treatment, or byencrusting.

When using the active compound combinations according to the invention,the application rates can be varied within a relatively wide range,depending on the kind of application. In the treatment of parts ofplants, the application rates of active compound combination aregenerally between 0.1 and 10,000 g/ha, preferably between 10 and 1000g/ha. In the treatment of seed, the application rates of active compoundcombination are generally between 0.001 and 50 g per kilogram of seed,preferably between 0.01 and 10 g per kilogram of seed. In the treatmentof the soil, the application rates of active compound combination aregenerally between 0.1 and 10,000 g/ha, preferably between 1 and 5000g/ha.

The good fungicidal activity of the active compound combinationsaccording to the invention is evident from the examples below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated according to S. R. Colby (“Calculating Synergistic andAntagonistic Responses of Herbicide Combinations”, Weeds 15, (1967),20-22) as follows:

If

-   X is the efficacy when applying active compound A at an application    rate of m g/ha,-   Y is the efficacy when applying active compound B at an application    rate of n g/ha, and-   E is the efficacy when applying the active compounds A and B at    application rates of m and n g/ha,    then $E = {X + Y - {\frac{X \cdot Y}{100}.}}$

The efficacy is calculated in %. 0% is an efficacy which corresponds tothat of the control, while an efficacy of 100% means that no infectionis observed.

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

The examples that follow illustrate the invention.

EXAMPLES Example 1

Erysiphe test (barley)/protective Solvent: 50 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound or a combination of active compound is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

1 day after the treatment, the plants are dusted with spores of Erysiphegraminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE 1 Erysiphe test (barley)/protective Active compoundEfficacy application rate in Active compound in g/ha % Known:

100  50 0 Known:

50 0 According to the invention: calc.* found

0 26 1:1*Calculated using Colby's formula

Example 2

Pyricularia test (rice)/protective (I) Solvent: 50 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound or a combination of active compound is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with an aqueous sporesuspension of Pyricularia oryzae. The plants are then placed in agreenhouse at 100% relative atmospheric humidity and 25° C.

Evaluation is carried out 4 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE 2 Pyricularia test (rice)/protective Active compoundEfficacy application rate in Active compound in g/ha % Known:

100  50 0 0 Known:

═50 29  Known:

100 0 Known:

100 29  According to the invention: calc.* found

29 50 1:1

 0 36 1:1

29 57 1:1*Calculated using Colby's formula

Example 3

Pyricularia Test (Rice)/Protective (II)

Rice grains (cultivar Nihonbare) were sown in plastic posts filled withsandy loam and grown in a greenhouse until they had reached the two-leafstage.

The pots with the rice were placed in plastic beakers with the testsolution and cultivated further in the greenhouse.

One or two weeks after the treatment with the test solution, the riceleaves were inoculated with Pyricularia spores (2.5×10⁵ spores/ml)

Evaluation was carried out about one week after the inoculation. 0%means an efficacy which corresponds to that of the control, whereas anefficacy of 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below. TABLE 3 Active compound Active application rate in Efficacyin Calculated compound g/10 acres % efficacy in %* Notes diclocymet 2083.2 — a (IX) 10 37.5 — a Compound (II) 100  0 — a (I) + (IX) 20 + 100100 83.2 a (I) + (IX) 10 + 100 97.6 37.5 a (I) 20 75 — b 10 12.6 — b(IX) 100  27.8 — b (I) + (IX) 20 + 100 88.1 82   b (I) + (IX) 10 + 10082.8 36.9 ba: inoculation one week after treatmentb: inoculation two weeks after treatment*using Colby's formula

1-5. (canceled)
 6. A fungicidal composition comprising an active compound combination consisting of (a) 2′-cyano-3,4-dichloroisothiazole-5-carboxanilide of formula (I)

(b) one or more of the compounds (1) N-[1-(4-chlorophenyl)ethyl]-2,2-dichloro-1-ethyl-3-methylcyclopropane-carboxamide of formula (II)

(2) a strobilurin of formula (III-a), (III-b), (III-c), or (III-d)

(3) a triazole of formula (IV-a), (IV-b), or (IV-c),

(4) a phenylurea of formula (V)

(5) a chlorophthalide of formula (VI)

(6) a hydrazine of formula (VII)

(7) a benzothiazole of formula (VIII)

(8) a cyanocarboxamide of formula (IX)

(9) a carboxamide of formula (X-a) or (X-b)

(10) a quinolone of formula (XI)

(11) a dithiolane of formula (XII)

(12) a phosphorous compound of formula (XIII)

(13) an iminoglycine of formula (XIV)

(c) one or more extenders and/or surfactants.
 7. A composition according to claim 6 wherein in the active compound combinations the weight ratio of the active compound of formula (I) to active compound of group (1) is between 1:0.1 and 1:20, active compound of group (2) is between 1:0.1 and 1:20, active compound of group (3) is between 1:0.01 and 1:50, active compound of group (4) is between 1:0.1 and 1:100, active compound of group (5) is between 1:0.1 and 1:100, active compound of group (6) is between 1:0.1 and 1:100, active compound of group (7) is between 1:0.1 and 1:100, active compound of group (8) is between 1:0.1 and 1:100, active compound of group (9) is between 1:0.1 and 1:100, active compound of group (10) is between 1:0.1 and 1:100, active compound of group (11) is between 1:0.1 and 1:100, active compound of group (12) is between 1:0.1 and 1:100, and active compound of group (13) is between 1:0.1 and 1:100.
 8. A method for controlling fungi comprising applying an effective amount of an active compound combination according to claim 6 to the fungi and/or their habitat.
 9. A process for preparing a fungicidal composition comprising mixing an active compound combination according to claim 6 with one or more extenders and/or surfactants. 